Nickel-Catalyzed Enantioselective Cross-Coupling of N‑Hydroxyphthalimide Esters with Vinyl Bromides

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis­(N,N-dimethylamino)­ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 ex...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (8), p.2150-2153
Main Authors: Suzuki, Naoyuki, Hofstra, Julie L, Poremba, Kelsey E, Reisman, Sarah E
Format: Article
Language:English
Subjects:
Catalysis
Esters - chemistry
Nickel - chemistry
Oxidation-Reduction
Phthalimides - chemistry
Stereoisomerism
Temperature
Vinyl Compounds - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis­(N,N-dimethylamino)­ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00793